 A series of pH dependent rhodamine analogs possessing an anilinomethyl moiety was developed and shown to exhibit a unique photophysical response to pH. These Anilinomethylrhodamines (AnMR) maintain a colorless, non-fluorescent spirocyclic structure at high pH. The spirocyclic structures open in mildly acidic conditions and are weakly fluorescent; however at very low pH, the fluorescence is greatly enhanced. Ultra/violet visible (Uv/vis), Fluorescence and Nuclear Magnetic Resonance (NMR) spectroscopy were used to explore the mechanistic details of this process. The equilibrium constants of these processes were correlated with Hammett equation, which show a linear response to substituent effects.

Anilinomethylrhodamines (AnMR) as pH sensitive probes with tunable photophysical properties

247th National Meeting (2014)

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